Sodium Hydroxide → HCID 57732106, compound

HRID 1808197Notes

Reaction equation

HRID 1808197 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[S:12]([N:15](CC1C=CC(OC)=CC=1OC)[C:16]1[S:17][C:18]([Cl:21])=[CH:19][N:20]=1)(=[O:14])=[O:13])[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[S:12]([NH:15][C:16]1[S:17][C:18]([Cl:21])=[CH:19][N:20]=1)(=[O:13])=[O:14])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57732072HCID 57732072, compound

Product 1

HCID 57732106HCID 57732106, compoundYield 146.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-chloro-4-{[(2,4-dimethoxybenzyl)(5-chloro-1,3-thiazol-2-yl)amino]sulfonyl}benzoate (Preparation 34, 3.2 g, 6.2 mmol, 1 eq) was suspended in 2.5M sodium hydroxide (7.4 ml, 18.6 mmol, 3 eq) and MeOH (40 ml) and the reaction mixture heated at 50° C. for 2 hours. The reaction mixture was concentrated in vacuo and the residue dissolved in 4M HCl in dioxane at 0° C. and the reaction mixture stirred at room temperature for 18 hours. The resulting precipitate was collected by filtration to yield the title compound as a white solid (3.2 g, 9.1 mmol, >100%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in 4M HCl in dioxane at 0° C.
  3. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-51700ab1e8af4aac9f3ccec6efe6b4a5
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

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